I placed the head of my cock at her anus, and started pressing it forward. I felt her sphincter instinctively tighten, fighting to keep out this unfamiliar intrusion. The trick in such a situation is not to increase the pressure - that will either result in the cock sliding off the target, or pain/injury to one or both parties. So I kept the pressure steady, and focused on keeping my cock right at her anus. The sphincter muscle can't sustain a tight contraction for long, and soon I could feel her resistance weakening. The sphincter slowly gave way in small steps, and at each weakening, my cock slid forward a few millimeters, aided by the lubricant and the steady pressure.

Then, as I was expecting, the sphincter suddenly gave way, and the head of my cock slid in easily, while she uttered a gasp of surprise. I held my cock in that position until she got used to my presence. Although this was rape play and I could be as rough as I wanted, I didn't want to ruin her first experience with anal and put her off that for life.

After I held my cock in position, only applying pressure at times when her sphincter tried to expel me, I could feel that the attempts to push me out were becoming less frequent. So I slowly slid my entire length inside her not-virgin-anymore anus while she drew a sharp breath between her clenched teeth.

She sighed as I slowly withdrew, until the head of my cock was all that was remaining inside her. I pushed in again, and the sharp in-drawn breaths and the relieved sighs sounded in tact with my rhythm.

After a few thrusts, I could feel her anus loosening up and becoming nice and slippery, and her breaths and sighs started turning in to soft moans. I ordered her to slide her palm underneath her and start massaging her clit. Soon, the room was filled with the sound of my rape victim's first ever anal orgasm.

To be continued

I held my cock in place, enjoying how the shudders of her first ever anal orgasm squeezed my cock, at first, rhythmically, and then spasmodically as her moans slowly tapered off to heavy breathing. I let her relax for a short while, and then ordered her to reach back with both hands and spread her ass cheeks apart as far as she could. I then let my cock slowly slide out of her, as she let out a soft sigh of relief.

With her hands still holding her ass spread, her just-devirginized anus was gaping open. I slid off the condom, aimed my cock at that slowly closing hole, and let my cum spurt. It splashed in and around her not-so-tight hole, dripping down her perineum to slide down her outer cunt lips before dripping slowly down her thighs.

I reached out and removed the soggy, balled up panties from her mouth. She was still breathing heavily, exhausted by the abuse and pleasure she had been experiencing. I knelt down, lifted each of her feet in turn, and slipped them in to the panties. I then gently pulled the panties up her legs, sweeping up the slowly dripping rivulets of cum on her thighs, until she was clad in her ruined panties with the crotch ripped open, and soaked in cunt juice, saliva and cum.

However, there was still one more ingredient missing to make those panties the perfect memento for that evening. As soon as her breathing slowed down, I was ready to provide her with one final humiliation.

I ordered her to slide down slowly from the bed in to a kneeling position, and from there on to all fours. I slid the belt off my jeans, and fashioned a make-shift collar around her neck (make sure you secure the belt properly if you do this - you don't want to accidentally strangle your sub if the loop tightens when you tug on it). Taking the collar in hand, I led her on all fours towards the bathroom. In the bathroom, I pulled her panties even further up her hips, so that her plump cunt lips protruded obscenely through the ripped crotch.

Meritus Mandarin is one of those swanky hotels which have a very spacious glass shower cubicle in the bathroom. I ordered her to crawl in to the shower cubicle, and closed the glass door. I told her that she is a dirty fuck bitch, and she should learn how to piss like one. I ordered her to lift up one leg, and piss against one of the glass sides of the shower cubicle. She hesitated, and then obeyed. With one leg lifted up and placed against the glass side, she closed her eyes and strained. It took a while, but finally a hissing stream of yellow piss spurted out between her cunt lips and splashed against the glass.

Her bladder was not very full, so it was limited to just a few splashes. After finishing, she put her leg down and remained still. I ordered her to stand up, opened the glass door and slipped the panties out of her. Now they were perfect - cunt juice, saliva, sperm and piss. Leaving her in the bathroom, I took the panties to the room, and put them inside a ziploc bag and sealed it.

When I went back in to the bathroom, she was standing there inside the shower cubicle, biting a fingernail. I got inside the shower cubicle and hugged her gently and pulled her to me. She melted in to me, letting me hold her. I slowly caressed her back, her hair and her buttocks, while I whispered to her that she was such a good sub, that she gave me so much pleasure, and thanked her for an unforgettable roleplay. As this was her first time doing something like this, and while cheating on her husband to boot, I was concerned that she would become overwhelmed by guilt, so I told her that there was nothing wrong in two adults enjoying themselves and exploring their fantasies, and that it was perfectly normal.

She leaned in to me, and I could feel her relaxing as I slowly stroked her hair and her skin and whispered soothing words in to her ear. I then slowly took off the tatters of her blouse and skirt, threw them on the floor of the bathroom, and closed the cubicle door. I turned the hand shower to a slightly warm temperature, and washed her. I soaped her skin, caressing the breasts and buttocks I had slapped and spanked, and gently rinsed away the suds.

After the shower, I toweled her dry, wrapped her in a bathrobe and led her back to the room. We cuddled on the couch, talking about things like places we would like to visit, the best places to eat char kway teow or bak kut teh in Singapore, why she doesn't like Louis Vuitton (at that time, every Singaporean girl wanted an LV bag) etc.

It was only after I felt her confidence building up and her mental state returning to normal, that I asked her whether she enjoyed the encounter. She told me that it was the most intense experience she has ever had, and that it exceeded all her expectations. She told me that she felt fear, excitement, humiliation, pain and pleasure all mixed together.

When she was dressed back in her street clothes we said our goodbyes, and I gave her the sealed ziploc bag to keep as a memento of our encounter.

======= The End ============

Yes, we still chat with each other online, but we have never met for a second encounter. With non-consensual roleplay, the first encounter between two strangers is always the most exciting. At a second encounter, you are no longer strangers, and you can anticipate each other. This makes it less exciting than that magical first time. And that magical first time is what I want her to remember.

Loved it. Keep writing.

Wow! That was actually quite amazing to me! The way you created a vivid picture of everything that happened and how you had the entire thing planned out! You must be a really gifted writer! Hope to read more about some of your meets!

Wow... That sounds a very intense encounter for the both of you. Very well written, I can really imagine how she must have felt.